


In a Perfect World...

by NefariousTillDeath



Category: Critical Role (Web Series)
Genre: Caleb is healthy in this fic, F/M, Other characters make brief appearances, and have a healthy relationship, but I didn't want to tag them because they don't have much screen time, cause I just want him to be okay
Language: English
Status: In-Progress
Published: 2018-12-01
Updated: 2019-07-12
Packaged: 2019-09-02 23:30:53
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 9
Words: 12,150
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16796863
Author URL: https://archiveofourown.org/users/NefariousTillDeath/pseuds/NefariousTillDeath
Summary: One-shots that will sort of fit in with the canon? Who knows what will happen, I just need to get some content out into this rarepair.





	1. You Were Always There

Jester lied awake in her bed, unable to sleep. Her conversation with Caleb the other day had helped her immensely, but she was still anxious and jumpy. With each passing day she liked the water less and less. She was eager to go home to her mother, but Caleb was right: they needed to stick with this to the end, for Fjord.

Gods above - then there was Fjord. What had happened to that happy little feeling that sprouted in her heart each time she saw his face? Presently, it seemed rather wilted and sickly. The more she got to know him the more she cared for him, but the more she was disillusioned with her idealization of him. Real life and Tusk Love weren’t quite the same thing, evidently. No, no matter how much she daydreamed about Fjord doing Oskar-y things, it didn’t change the fact that he was a very different man from the hearthrob in her new favorite book. 

That was okay, really. Of course Jester didn’t expect him to change himself for the sake of her wiles. She wanted him to flourish in his own place, to be the person he was meant to be, and grab his fate by the reigns. She wanted to see him achieve his goals, find his answers, and be happy. She just didn’t see a way for her to be a part of that for him. That part was, admittedly, less okay.

She felt now that a little part of her had always known Fjord would never reciprocate her flirtatious advances, and yet it hurt. She needed someone to sit with, to hold her, and tell her it was okay to get just a little too caught up in her feelings. She wanted someone to assure her that what she’d felt wasn’t foolish, only in vain. The problem wasn’t failing to romance Fjord - it was whether or not she’d made a fool of herself in the process.

Before Jester knew what she was doing, she found herself at the door to Caleb and Nott’s room in the greasy wharfside tavern the Nein and Avantika’s crew were holed up in. She hesitated for a moment, wondering if she should just go back to her room when suddenly the door opened, and she stood face-to-face with Caleb. He was surprised at the sight of Jester in her bedclothes, eyes puffy and red from crying.

“Jester,” he stammered, eyeing her in confusion, “what is the matter?”

“Oh, it’s nothing really,” she said, trying to shrug off her obvious upset, “I just wanted to see if you, um, if you-” she stumbled as she lost her composure, “I need to talk to somebody!”

She fell into Caleb, who stood stunned before throwing his arms around her in an awkward hug. His brain was running a million miles a minute trying to figure out what was wrong and what to do as Jester cried into his chest.

“Ja, why don’t we… come in here?” he fumbled as he lead Jester into the room. 

Nott rolled over, looking grouchy at having been awoken in the middle of the night. At Caleb’s pleading look, she grabbed Frumpkin and sneaked out of the room, sights set on Jester’s now-empty bed. 

Caleb sat Jester down on Nott’s abandoned bunk and knelt before her so he could see her face-to-face. He took a moment to clear his mind before he spoke. “Jester, what is this crying all of a sudden? Did something happen?”

Jester’s face was streaked with messy tears. Caleb couldn’t tell tears from snot. Without a second thought, he passed her one of the cleaner rags from his pocket to clean up with, and she sniffled and sobbed as she rubbed the coarse cloth over her face. 

“Oh, Cayleb,” she cried, “I’m sorry. I just feel so stupid! And I was all alone, thinking about how I just wanted a hug, and then I was here, and then I was crying, and I probably woke you up, and now you’re probably mad at me, and don’t want to be my friend anymore, and-”

“Nein, Blueberry,” he said, squeezing her shoulders in reassurance, “I was reading. Actually, I was going to go to the bathroom - no, that’s not the point. The point is I’m not mad at you.”

“Really?” she asked, fresh tears spilling down her cheeks.

“Really,” he whispered as he hugged her tight. She settled into his embrace. The hug went on for much longer than he’d expected; he decided she must need a nice long hug, so he did the best he could.

“I feel so stupid for all that stuff with Fjord,” she eventually choked out. “I really thought he liked me, and I couldn’t stop flirting with him because that’s what you do when you like someone, and now I think he really doesn’t like me, and - augh, Cay-leb, I’m so stupid!”

“Everyone has feelings for people sometimes,” Caleb said, the words coming out a little awkward and not exactly how he intended. “I don’t think it is a good idea to be embarrassed for liking someone.”

“No,” she sniffed, still clinging tight to him, “I’m stupid for I wasting so much time on stupid Fjord, especially when someone I loved more was there the whole time.”

“I wouldn’t worry about that too much either,” Caleb said, confused by her statement but still wanting to be supportive. “If you love them, they must be kind. They can’t be upset with you over this.”

“I feel like maybe I treated him badly because I was so head-over-heels for Fjord. Maybe I ignored him too much and told myself I didn’t like him because of Fjord, maybe,” she sputtered.

“You could apologize to him,” Caleb offered, still stumped about Jester’s worry. “Maybe you’ll find out he was not so bothered as you think, ja?”

Jester sniffled, and giggled slightly, “Oh, come on Cayleb, if you know why don’t you just say so!”

“I, em,” Caleb started, but then realization hit him like a ton of bricks: she was talking about him.

“Oh, Jester,” he said, pausing for a moment to think about what he was going to say, “I did not ever feel that you treated me badly.”

Jester looked up at him, laughed nervously, and smiled before she leapt at him with a hug. The force of her throwing herself at him toppled them to the floor, and Caleb collided with the hard wooden slats below. As he groaned, Jester giggled and hugged him tight. He shook his head and threw his arms around her, holding her in a warm embrace. He laughed too.

Caleb yawned. “Maybe we should go to sleep, ja?”

“Yeah, I think we should do that. I don’t want to wake up Nott again though…”

“I think you could sleep in her bed,” Caleb said, stifling another yawn.

He managed to stand up with Jester still in his arms and tucked her into Nott’s bed, pulling the rough covers up to her sleepy smiling face. He hesitated for a moment, his cheeks flushed bright red under his scruffy beard, before kissing her softly on the forehead. He retired to his bed and blew out the lantern.

“Cayleb?” Jester asked into the darkness.

“Ja?”

“Can I hold your hand?”

Caleb grinned. “Ja, Liebling.” He reached his hand across the narrow space between the two small beds and his rough hand met hers and held it tight.

“Goodnight, Cayleb.”

“Goodnight, Jester,” he whispered.


	2. A Kiss Under the Stars

**Summary for the Chapter:**

> (Post-E43) Jester and Caleb stargaze on the way to Nicodranis.

“Only two days away from Nicodranis now, Jester,” Caduceus said nonchalantly as he poured over the maps Fjord had scattered across the desk in his captain’s quarters. 

“I know!” Jester exclaimed, “Oh, Deuce, we’re going home! We’re going to see my mom, and tell her about our crazy adventure, and how we fought Avantika - and killed her!” 

“Technically the Plank King killed her,” Caduceus replied without looking up from the maps.

“Oh, psh,” Jester huffed, “we pretty much made it happen though!”

Caduceus pondered that for a moment before responding, “I suppose that’s true.”

“Do you think we’ll get in trouble when we get there?” Jester asked, suddenly concerned.

“I think if we can sit down and have a nice, rational discussion with anyone who’s upset, we could come to some sort of understanding, don’t you?” Caduceus mused, having finally abandoned the maps for the night. 

He stood from the desk, crouching slightly in the too-low space, and walked out of the quarters with Jester. He stood tall and stretched his neck in the frigid night air, sighing contentedly. He and Jester had been chatting for some time now, and staying in that cramped space for so long had really tightened up his back and shoulders. He yawned wide, showing off his tea-stained molars. 

“I think I’m gonna turn in for the night. Got a long day ahead of us tomorrow,” he said quietly. 

“Goodnight, Caduceus!” Jester replied, grinning wide at him.

A cold wind rushed past as he made his way below deck, and Jester, standing out on the deck, was struck with chills. She pulled an enormous scarf out of her haversack and donned it like a thick hood. She didn’t care to go below deck just yet - she wanted to see what Caleb was up to up on the upper deck of the bow.

She made her way up to where Caleb was, lying on his back beneath the head sails, gazing at the stars. Frumpkin, who had recently been turned back into a cat, was curled up inside his coat. It seemed Jester wasn’t the only one bothered by the cold. She laid down next to Caleb and watched familiar stars float by as the ship sailed below them.

“It’s pretty cold out here,” Caleb said softly. “Do you want something warmer to wear?”

“I’m okay,” Jester lied right as a fresh chill ran through her, giving her away.

“Ja, okay,” Caleb huffed as he uncrossed his arms and held them open toward her.

Jester settled next to him, and Caleb pulled her close as he did his best to wrap her in his jacket with him. Frumpkin grumbled and disappeared, leaving a little more space in the old coat. Jester was surprised how warm it was inside - she didn’t think the coat had given Caleb that much protection from the elements, but it turned out to be quite cozy. She snuggled in with him, still watching the stars.

“Thank you,” she whispered. Caleb only squeezed her in response.

“I know it is a little silly to be out in the cold,” he began with a contented sigh, “but I like to watch the stars. It’s so different to watch them when you’re moving than when you’re in the dirt.”

“It’s sort of like they’re dancing, sort of,” Jester mused, her voice muffled by her scarf.

Caleb watched her as she talked, saw how the reflections of the stars twinkled back at him in her eyes. He felt a warm blush rising from his cheeks to his ears, and he was grateful for his beard and wild hair. She looked so perfectly content, awestruck by the same stars they’d seen every night. He loved how easily she saw beauty in the world.

“Do you really like me, Cayleb?” she asked, her gaze still fixed on the stars above.

Caleb reached for her scarf in response, pulling it away just enough to see her whole face.

“What are you doing?” she giggled, cocking a brow.

“It would be a little difficult to kiss you with your scarf like that, you know,” he said, matter-of-fact.

Jester grinned at him and turned to face him as he pulled her in close, and their lips met. It was soft and sweet; Caleb’s beard tickled Jester’s face, and she couldn’t help but giggle. As their lips parted, Caleb’s forehead met Jester’s, and he just held her close for a moment. His heart was pounding wildly. He laughed as she pressed a hand to his chest and felt it too. 

“I’ve never kissed someone with a beard before,” she whispered. “You know, it tickles a lot!”

“Should I ask Yasha to shave it again?” he asked, a wide smile painted on his face.

“No!” Jester exclaimed as she put her hands around his face, her fingers settling in his auburn scruff. “I’d make you stick it all back on.”

“I won’t do that, then,” he said, giving her a serious look with a goofy grin.

They lied in silence for a little while, enjoying each other’s company and trying to stay warm despite the frigid ocean air. Caleb’s heart had slowed, and Jester’s breathing matched it. She snuggled into him as the cold started to seep in through the front of Caleb’s coat. He wrapped his arms around her again, holding her close.

Their noses brushed, and Jester’s lips touched Caleb’s once more. She kissed him again, a little more deeply than before now that they had tipped the iceberg. Her hands still held his face close, her fingers occasionally straying to weave through a flyaway strand of his hair. She pulled away after a minute or so and rested her head against Caleb’s chest with a contented sigh. 

“Liebling, if we stay out here much longer, you will turn to ice.” 

“Only if you let me snuggle you all night,” Jester yawned. Caleb could see her grin, even as she tried to hide her face from him.

“For you, Little Blueberry, anything.”


	3. When in Xhorhas

**Summary for the Chapter:**

> Jester and Caleb haven't had time alone together since Nicodranas, and they miss each other.

Xhorhas was more than Caleb could have imagined - more violent, lawless, dangerous. Death trailed faithfully, patiently waiting for them to make a wrong move and fall into its gaping maw. Yet the Mighty Nein prevailed. They’d come close more times than Caleb liked; it had been at his hands that more than one of them had gazed at death. He couldn’t shake the guilt that ate away at him. He knew it wasn’t his fault, but it bothered him that he’d been charmed so easily. He was bound and determined not to let it happen again. 

That was two weeks ago. They’d almost made it to Ghor Dranas; a few more days and they’d reach their destination. They’d stopped in a city Yasha spoke highly of - at least, as highly as one could speak of a Xhorhasian city. Caleb was grateful they had a decent tavern and inn. He’d never wanted to sleep in a clean, dry place so badly until now. 

He collapsed on the small, low bed and sighed. It wasn’t the most comfortable bed in the world, but it was a fine reprieve from stone and wasteland. A fine reprieve from sleeping in Leomund’s Hut with his compatriots. It wasn’t the first time he’d bunked alone, but it was always strange to be without Nott. He missed Jester, too. He hadn’t had time alone with her since Nicodranas. She was in the room with Beau, Nott, and Yasha upstairs, though, and Caleb didn’t want to arouse suspicion amongst the Nein. 

He took out a wire anyway. He cast message and spoke softly into his cupped hands. 

“I miss you. Would you come see me, Blueberry?” He paused. “You can reply to this message.”

He heard Jester giggle on the other end. He laid back on the pillow and rested his head on his arms as if sunning himself on a summer day. His books were still strapped beneath his arms, exposed now with his coat discarded on the floor. 

The door opened quietly and suddenly Jester leapt onto the bed, nearly bouncing Caleb off of it. She scrambled to grab him and burst out laughing. He couldn’t help but laugh back at her before pulling her close for a kiss.

“Caleb,” Jester muttered, their lips still locked, “your books.”

“Oh, sorry, Liebling.” He sat up and reached for the clasp, but Jester stopped him. 

“Let me,” she said softly. Caleb noticed the mischievous look in her eye. 

Jester undid the buckles keeping Caleb’s precious tomes in place, and the leather straps fell off him. He grabbed the holster and gently lowered it onto his coat before embracing her and pushing her back onto the bed. She giggled as Caleb showered her face and neck with kisses, his beard tickling her as he went. Jester pulled his face back to hers and gazed at him for some time. 

“I really, really, really missed you.”

“Me too,” Caleb breathed. His hands left her face, one drifting to her back and the other her waist. He pulled her up and kissed her, hungrily this time. She held him close and ran her hands through his travel-dirtied hair. 

“You know, there’s this thing called a ‘bath,’ you should try it maybe.”

Caleb glanced over Jester, her hair and skin just as travel-worn as his own, and grinned. “Am I so stinky again?” Jester just laughed.

A few silver pieces secured a bath in one of the small rooms downstairs where a large wooden tub filled to the brim with hot water awaited them. Caleb slipped his shirt and boots off quickly, but paused to help Jester undo her dress. His hands were gentle and steady, although his heart was beating wildly. They’d been naked before at the bath house, but that was a communal activity. This was far more intimate, and Caleb was nervous and excited all at once. 

He unbuttoned the last clasp of her dress and it fell gracefully to the floor around Jester’s feet, leaving her only in her shift. She pulled the thin fabric off over her head and waited for Caleb to follow suit, her tail softly flicking two and fro past her ankles. Caleb didn’t mean to seem boorish, but it was something else to see her like this. This was a kind of vulnerability and intimacy they’d not yet shared. 

Caleb came to his senses and stripped off his trousers and underwear and climbed in the tub. The warm water cradled him and eased his aching muscles. Jester followed and lied against him, her soft blue body cool against his skin even in the hot bath. She rested her head on his chest, her horns just brushing his chin and neck. Caleb gingerly rested his hands on her waist. Her feet brushed past his, and Caleb couldn’t help but brush back. 

He reached for a glass jar filled with some heavily-perfumed soap and poured some in his hands before setting to work, gently working it through her hair.

“I need to apologize to you,” he said as he rinsed the soap from her navy hair. “For what I did in the well.”

“Cayleb-”

“No, Jester, I need to apologize. I know I was not in control of myself, but I was deceived because of my own insecurities. I believed those devils because I doubted everyone and… I doubted you,” he paused, the words became difficult to say, “I need to ask your forgiveness for not trusting you.”

“Of course I forgive you, Cayleb, of course,” she said without hesitation. “You’re my friend and I love you.”

“You are too good, Liebling,” he whispered as he pressed a kiss to her head. He rinsed the last of the soap from her hair. “Will you wash my hair?”

Jester happily returned the favor, laying herself comfortably on her stomach so she could get to his hair. She couldn’t help but peck him on the cheeks and forehead as she went, slowly washing his auburn locks. 

“Caleb?” Jester dumped a pitcher of water over Caleb’s head; his hair fell over his face, obscuring Jester. 

“Ja?” He replied, brushing his hair back with one hand. 

“Do you think we’ll ever get to stay in one place for a while?” There was a note of sadness in her voice. 

“Um… I’m not sure. I would like to hope so, but our lives - the Nein, I mean, all of us - there’s so much yet we have not done.” He stopped as Jester rested her head on his chest, her arms casually wrapped around his waist. 

Caleb held her, one hand on her back and the other in her hair, and kissed her forehead. He began drawing circles on the small of her back, lazily running his fingers across the span of her cool skin. 

“Liebling,” his voice was soft but sure, “I will do everything in my power to see that day for us.”

She gazed up at him and a faint smile pulled at the corners of her mouth. 

“This bath is getting cold, and I would like to bed for the night,” Caleb said quietly. Jester nodded in agreement. 

They left the bath, dried themselves, and returned to Caleb’s room dressed in their underclothes. Jester crawled into the little bed and watched Caleb as he folded their clothes expertly. He laid his books atop the stack of day clothes and finally made his way to the bed. He lied beside Jester, holding her body close to his. Jester’s tail wound around Caleb’s legs. Caleb tucked one arm beneath the pillow and the other across her. She laced her fingers with his and settled into the curve of his lithe body. 

“Someday, Jester, we will have a simple life.”

“I know,” she said. “But for now, adventure.”


	4. Stories

**Summary for the Chapter:**

> Jester reads Caleb her favorite childhood book. (Suggested by @goggles-girl on tumblr <3 tysm)

Jester always had her nose in a book. Most of the time it was a smutty book she’d knicked from Caleb, but every now and then he’d see her with an unfamiliar title. Caleb also often found himself turning the pages of a good book, usually the smutty books he picked up for “historical research,” at least until Jester stole them from him. She’d always return them after a while, illustrations free of charge. The day he saw her with a novella wearing a brightly-colored jacket was the first time he ever asked her what she was reading.

“It’s a book my mama gave me when I was a le-etle baby!” she exclaimed, presenting it proudly. The cover was red and blue, emblazoned with gold leaf, and depicted a lion carrying a patterned banner. There was no text on the exterior, so Caleb had no inclination what sort of story could be found inside.

“What is it?”

Jester ran a finger down the spine fondly. “It’s about this super-hot knight who travels across the whole world to find a princess who’s been locked away in a huge castle by a witch, and he searches everywhere for this girl, and when he finally finds her, he finds out that she is the witch! But then they like talk, and they fall in love, and they live happily ever after. It’s such a good book, Cayleb. You should totally read it sometime.”

“That does sound like quite a story,” he said as he sat beside her. He peeked over her shoulder to get a look at the pages and was surprised to see large text and colorful illustrations quite unlike those Jester left in his books.

“It’s my favorite book. I take it with me everywhere we go,” she said, flourishing the book for emphasis.

“Pretty risky to take something so precious where we go,” Caleb joked. 

Jester grew somber as she slowly paged through the little book. “I know.”

She paused on the last page where the words “they lived happily ever after” were calligraphed in common above a drawing of the human knight holding hands with the witch princess, a tiefling.

“It was the first gift mama every gave me, and I miss her a little less whenever I read it.” There was an overwhelming tone of longing in Jester’s voice as she gazed at the little drawing. 

That night Caleb made it to bed long before Jester. He watched her as she paced around the room, moving from bag to bag relocating clothes, food, and other supplies they’d bought at the market that day. He caught a glimpse of her book poking out of the Haversack when she rifled through it in search of gemstones and other jewelry to trade the following day. 

“Blueberry?” he asked, interrupting her furious digging. “Would you read that book to me, the one your mother gave you?”

“Ooh, of course!” She snatched the book and handed it to Caleb before changing into her bedclothes and climbing in bed with him.

She took the book back and began to read.

“Once upon a time, in a land far away, a young knight set out on a quest to find the kingdom’s long-lost princess.

The princess, said to be gentle and kind, had been stolen away by an evil witch as a baby. No explorer or knight or prince had ever found her, and after twenty years the kingdom began to give up hope.

One knight refused to give up! He trained every day from dawn until dusk so he could one day rescue the princess.

He travelled far and wide across every continent and sea in search of her. He left no dark castle unsearched, no mountain caves unexplored, no stone unturned. But he didn’t find her.

He wept and cursed himself because he thought it was his fault he couldn’t find the princess, and he wanted to return home. 

In the night, his ship was blown off course by a terrible storm, and they landed on an island that wasn’t on any of the knight’s maps. In the distance, he could see a castle keep.

The knight journeyed to the castle and entered to find a powerful witch inside! He called out to her and demanded she return the princess unharmed. The witch began to cry, and the knight was confused.

The witch told the knight she was the long-lost princess, and she’d been trapped on this island since she was little by a magic spell she’d cast by mistake!

The knight had broken the spell by travelling where no person ever travelled in his relentless search for her, and when they returned to the kingdom he was called a hero for rescuing her.

He fell desperately in love with her, and when he confessed to the princess she took his hand in marriage.

They lived happily ever after.”

“You are right, Liebling,” Caleb said softly, “that is a very good book.”

“Mama always said I was the princess, and someday a good person would find me, and even though it would be super duper hard because I had to hide, they would find me and we would go on a journey like the knight and the princess.”

“Your mother is a wise woman,” Caleb said seriously, his wide grin deceiving his sobriety.

“I wondered if I would find a knight when I left home,” Jester mused.

“Did you?” 

“Nah, just a stinky wizard with a super cute cat.”

“You, Mäuschen, are lucky to be cute, you are so cruel!” Caleb growled as he grabbed Jester tight and tickled her mercilessly. She struggled against him, but he didn’t relent until tears were streaming from her eyes and she couldn’t breathe. She poked him in the side in retaliation, her scowl betrayed by the smile growing out of it.

“I would pick you over some stuck-up knight every time,” Jester said as she gazed at Caleb.

“We’ll need to write a different book.”


	5. A First Time for Everything

They couldn’t have been in Xhorhas for more than a month now, but to Jester it felt an eternity. It wasn’t all bad - they got to see so much of Yasha’s home, meet so many interesting people, and go on so many thrilling adventures - but she was starting to get tired of being in the same small place for so long. The Kryn had been kind enough to provide for them a warm place to stay and good food to eat, so she really couldn’t complain, but she’d be lying if she said she didn’t feel stagnant. 

So when Caleb asked her to accompany him on a research adventure she didn’t hesitate to agree and collect her things from her room.

“Ja, Waccoh wants me to do a little digging in the eastern part of town, and I thought I should bring a little muscle with me in case the locals get too nosey,” Caleb explained to Fjord and Beau. Caduceus nodded, and Yasha gave him a small thumbs up.

“How long d’ya think it’ll take?” Fjord asked.

“Hopefully just a day or two,” Caleb said, rubbing the back of his neck. “I don’t particularly like wandering around here without the group.”

“Jester’ll protect you from any shithead who gets in your way, won’t ya, Jessie?” Beau wrapped her arm around Jester’s shoulders and gave her a shake.

“Well, we’ll plan to be back tomorrow then. If something changes, we will let you know, okay?” 

And with that, Caleb and Jester were off.

Travelling through Rosohna was pleasant enough, even if Jester had already seen a great deal of it. Admittedly, she hadn’t yet gone as far east as they were going to research for Professor Waccoh, and Jester was secretly excited. They opted out of taking one of the Moorbounders and left them instead in Caduceus’ capable hands. 

The journey from their inn to the eastern area wasn’t more than an hour’s walk, but they’d left a little late in the day and Jester’s stomach was wailing for food. Caleb looked more on-edge than normal, but Jester was too hungry to notice.

“What’s the plan, Cayleb?”

“I think we should find the inn first, and then we will worry about getting the information for Waccoh,” Caleb said as he lead Jester down a narrow alleyway.

“You should be fine, little Blueberry, but I need a disguise.” Caleb closed his eyes and focused his energy. He glowed softly and Jester watched as horns curled out of his temples and his skin darkened to a cool midnight blue. His eyes flashed open, solid red, and two pointed teeth poked out from his upper lip. His false tail flicked lazily back and forth, and he’d disguised his traveling clothes for a slightly-higher-end look. 

“Oooh, Cayleb, that’s a nice look on you!” Jester teased, lacing her arm through his.

“Maybe I should wear it more often?” he asked sweetly.

“It is very beautiful,” she said, “but I like you best the way you are, Cayleb.”

They continued down the busy streets, no longer turning heads. Caleb lead Jester to a large building with a tall stone wall around the perimeter. It was a hotel - a proper hotel, not an inn or tavern house - milling with people. It was subtly elegant, just what Jester had come to expect from Rosohna. There were a few Drow and Half-Orcs sitting out in the dark courtyard, but Jester didn’t see many other people out and about. 

Inside, the walls were decorated with fantastic, shimmering tapestries featuring the flora and fauna of Rosohna. Golden lanterns set with crystal and quartz hung from the walls as discreet sconces and from the ceiling as elaborate chandeliers. The black-and-silver woven rugs that lined the halls and entryway grounded the room, tying it all together into a breathtaking scene.

Caleb made his way to a Drow standing at a lectern and requested the reservation made by Professor Waccoh for Caleb Widogast, and the Drow beckoned them to follow him into the chalet. Jester marveled at the architecture; it was not all unlike that which she’d seen in the castle, and she wondered if it had once served as part of the keep. It was a little too far away, but one could never know for sure.

Caleb dropped his disguise as soon as the door was shut and latched, and he breathed a contented, relieved sigh. He held his arms out and Jester hugged him tight. He kissed her forehead, then rested his forehead in the space between her horns and breathed her in. She laughed and squeezed him, and she tried not to laugh as his beard tickled her face. He suddenly grabbed her and lifted her in an excited twirl before bringing her back down to earth with a kiss. 

He didn’t pull away; instead he ran one hand through her hair and wrapped the other around her. She rested her arms on his shoulders and kissed him back, pleasantly surprised by this sudden burst of romantic energy. She was a little disappointed when he finally let her go, but she quickly recovered as he stared into her eyes and his crinkled at the edges as he smiled.

“Jester,” he whispered just loud enough for her to hear, “I love you more than anything in the world.”

“Oh, Cayleb…”

“Let me finish?” he asked. Jester just rolled her eyes and smiled. “For the first time since we met, we have time alone together, really alone…” He paused. Now Jester did notice his nervousness. “May I… spend tonight with you?”

Jester’s heart raced, and she felt her face flush as warmth crept across her face and down her neck. Hadn’t she just told Beau she didn’t know love outside of a romance novel? Was that what Caleb expected? Caleb’s face sobered slightly as she hesitated.

“I’m sorry, Jester, I should not have asked this of you-”

“Yes,” she interjected. Now Caleb’s face burned red.

“But, um, you know, I don’t really, I mean I know what I’m doing, obviously, like I know all kinds of stuff and-”

“Jester,” Caleb stopped her, gently taking her by the arm and holding her hands, “I do not have any wild expectations. I just want you.”

Jester looked at him and smiled. She trusted him.

“Can you put out the lanterns?” She asked, still a touch sheepish.

“Anything for you, Liebling.”

When the room was dark and Jester could only just make out the shape of Caleb, she reached out to him and held him as they kissed. When he laid her on the bed, still holding her close, her heart felt light and heavy all at once as it drummed away. Caleb let her set the pace; they lied in bed for some time, kissing and whispering to each other occasionally. Jester ran her fingers through his hair and traced the line of his jaw. She could only just make out the details of his face in the dark, but he looked handsome as ever.

“Should I take your shirt off?” she mumbled.

“If that is what you’d like to do,” Caleb said softly.

Jester struggled to get the tunic off of him, and she grew ever-conscious of her movements as she tried to get him out of the loose fabric. When she finally pulled the shirt over his head, he took it gently from her and tossed it to the floor. He wrapped his arms around her once more, and the familiar sensation of his skin against hers suddenly felt so very new. 

“I undid my dress while you put out the lanterns.” Jester screwed up her face at herself, frustrated with her awkwardness. She steeled her nerves and breathed deeply. “Could you get me out of it?”

Caleb shifted and lifted Jester away from the bed and against his body, but as he settled in to undress her, she cried out in pain.

“Ow, ow, ow, ow! Cayleb… your knee… is on my tail!”

He quickly moved his legs and let her free herself before asking her if he could continue. They both laughed, and Jester playfully shoved him a bit before he tackled her back onto the sheets.

From beginning to end, it was new and clumsy and gentle, Jester fumbled around Caleb’s body, not entirely sure what to do with him. Caleb didn’t push her once, only doing what she said she wanted to do and stopping when she asked him to. When she accidentally jabbed him in the eye with her horn he chuckled and tickled her; when Caleb’s arm slipped and he fell on her she cried from laughing as he sat back on his heels and laughed at himself. As they stumbled through their first night together, the awkwardness slowly melted away, replaced with a sense of deeper understanding. 

Jester’s body was cool against Caleb’s as they cuddled, her body pressed into his and her tail between his legs as they spooned. Jester struggled to stay awake as Caleb drew little swirls on her stomach. 

Just as her eyes were starting to flutter shut, they flashed open and she sat up to face Caleb, nearly startling him half to death.

“We didn’t do any snooping!” she exclaimed.

Caleb looked puzzled.

“For Professor Waccoh! Cayleb! What are we going to do?”

“Oh,” Caleb sighed, “I got that earlier today. It was actually in a book she gave me. I just used it as an excuse to give us some time alone.”

“Oh, Cayleb!” Jester yelled, pretending to be angry as she tackled him. He laughed as she pummeled him with her pillow, her tail whipping back and forth playfully.

She flopped back onto the bed and Caleb snaked his arms around her once more. “Can we go to sleep now?” Jester yawned.

“Ja, little Blueberry.” Caleb nuzzled her neck and cheeks and settled in with her.

They returned to the inn where the Nein were staying in the morning. Caleb went out back to check on Jannick and Yarnball while Jester retreated inside to check on Sprinkle and Nugget. Her friends, except Beau, were seated in the tavern eating a hearty breakfast. Jester waved to them and headed upstairs. Just as she opened the door to hers and Beau’s room, the door opened and she was face to face with her long-time roommate.

“Hey, Jester, I didn’t think you’d get back so soon! How’d it go? Did you guys find anything cool? Dig up any wild secrets?”

“Oh, haha, yeah, crazy stuff. So much… secret things…” she trailed off as she yawned.

“Little too much late-night investigation, huh?”

Jester’s face flushed. “Haha, yeah, I guess I’m just a little tired - because of all the snooping, not because anything happened -- okay, goodnight, Beau!” Jester pushed past Beau and slammed the door behind her. 

Beau’s brow furrowed as she sleepily considered what Jester was on about, utterly and totally confused. She shrugged and continued on her way down to breakfast. She took the seat between Nott and Caduceus and started shovelling food into her mouth like it was her last meal. She tuned out the chatter in her morning stupor, letting her friends’ voices become a familiar white noise.

She was chowing down on bacon and seared fish when suddenly her eyes flashed wide and she sprayed half-chewed food across the table and all over Fjord.

“Holy fuckin’ shit.”

“What in the hell?” Fjord growled as he wildly brushed Beau’s food off of himself.

“Are you okay?” Caduceus’ arms were outstretched, ready to catch Beau or maybe cast a healing spell if she needed one.

“Oh, me? Yup, uh, yeah, totally fine.” She jammed another fish in her mouth. “Sorry Fjord.”

Fjord just stared daggers at her from the other side of the table.


	6. Kindness and Happiness

So much had happened since the Nein moved into the Xhorhaus. 

None of it seemed simple or straightforward to Jester. She couldn’t wrap her mind around the chaos: the war, all the double-agents, all the secrets, the whispers… She was doing everything in her power to keep spirits high. Someone had to be their rock, after all, and she was so good at it. 

She and Caduceus baked sweet cinnamon desserts for everyone that first night back home. She even sent some to the Lucid Bastion for Essek and the Bright Queen. Fjord had been skeptical, but Jester didn’t care. It didn’t matter what they actually did with the goods so long as it gave everyone a laugh. She just smiled and made something up about Essek looking like he needed a doughnut. 

When Yasha asked Jester to paint some more around the house, she did so without a second thought. After a few days of hard work, almost the whole house was decorated with the most beautiful scenes Yasha had ever seen. Jester had hardly slept at all, often dozing off with a brush in her hand, desperately trying to make Yasha happy. She cast disguise self whenever she looked too ragged so as to not let anyone know how haggard she was.

Veth and Yeza were so worried about their son, and Jester didn’t really know what to do to help with it. She tried to be as helpful as she could, often spending hours on end assisting them in the lab. She didn’t understand a single thing they were talking about, but she did her best to be a good apprentice. Every time she made a mistake, they laughed. She may have started making mistakes on purpose.

Jester suspected Beau was hiding her unease as well, but she didn’t say anything to Beau about it. Instead, she challenged Beau to feats of strength -- arm wrestling, who could carry the most vegetables down from Caduceus’ garden, tug-of-war with the Moorbounders -- and would spend their downtime reading Caleb’s books. 

Fjord… well Fjord was a whole problem on his own. Ever since he’d kissed her cheek back at the Overcrow, he’d been especially interested in her. She wasn’t sure where all this romantic confidence had come from all of a sudden, but she felt it was entirely too late. She did her best to seem airy and return his advances as much as she could; she wouldn’t lead him on too far if it really got down to it. For now, she did what she could to play hard-to-get. Whatever heart-breaking she had to do after that, well, that was a problem for another day.

Then there was Caleb. He was easy to cheer up. All she had to do was sneak a kiss when he wasn’t expecting it, stick her tongue out at Frumpkin when he blepped, or generally pester him and he would grin and blush. It was easy to see that now that he’d shaved his beard again. Jester preferred the beard, but she wouldn’t demand it of him. 

After a particularly-exhausting day, after everyone had gone off to bed, Jester sneaked out of her and Beau’s room, tiptoed down the stairs, and quietly made her way to Caleb’s room. She was glad he was the only one down here, because she made enough noise accidentally that she certainly would have awoken anyone on this floor. 

Caleb was, of course, still awake when Jester eased his bedroom door open and crept inside. He looked up from his book and fixed her with a concerned glare. He closed the book and stood from his tome-laden desk, crossing the space between them in an instant to embrace her. As he absentmindedly played with her hair, she leaned against him and sighed deeply. She was tired.

“Liebling,” he said softly, “you do not have to carry this burden on your own.”

Jester yawned and lazily wrapped her arms around Caleb’s waist. “It’s not a burden… I love them, more than anything. I would do anything to keep them happy, Cayleb.”

“You’re much better to them when you are also happy.” Caleb said as he pressed a gentle kiss to her cool, blue forehead. “You’re better to yourself, too.”

“I know, but… I just can’t stand to see anyone sad. Not now. Everything is so tense, like we’re all waiting for something terrible to happen!” Jester’s voice strained against another yawn, and tears of exhaustion beaded at the corners of her eyes. “I can’t just wait around for everything to go bad… I have to make sure they’re okay.”

Caleb walked Jester to his bed, removed her dress and shift, and clothed her in one of his nicer, softer shirts. It hung almost to her knees, and he’d had to roll the sleeves a few times so her hands wouldn’t be lost in them. He tucked her in before donning his own bedclothes and settling in behind her. He held her close, showering gentle kisses across her hair, neck, and shoulders. She laced her fingers between his where they lay across her stomach. 

“Jester, you are not going to help anyone if you work yourself to death.” Caleb’s voice was laden with concern. She felt a pang of guilt in her chest. She didn’t say anything.

“I know this is hard for you. You love them all -- I love them too. I want them to be happy as much as you do, but I can’t do that by making myself miserable.”

Jester turned around to face him. She gazed into his striking blue eyes. The lantern light from the desk reflected in them, casting a warm glow across his clean-shaven face. She ran a thumb across his cheekbone as she considered what he said. He only looked back at her. 

Jester curled up against him as hot tears trickled down her face, quickly wetting his shirt. Caleb slowly rubbed her back and held her close while she cried. Whether it was from exhaustion or stress or relief he didn’t know. He would just give her a safe place to cry and let her rest. 

Some time later she dozed off. Caleb couldn’t sleep, though; he was so worried about Jester but didn’t know what to do to help her. He had never been much good at emotional support, even when he was younger. Now he felt utterly incapable, and it infuriated him. 

Despite Jester’s cool skin, Caleb grew hot under the heavy covers. Rather than try to escape the quilts and risk chilling Jester, he wriggled out of his shirt and tossed it to the floor. 

Much better, he thought. He settled back in and closed his eyes, ready to doze off at long last. He’d have to sleep until midday to get a full night’s rest. His breathing was just starting to fall in sync with Jester’s when a little bell went off in his head and his eyes flicked open and fixed on the door. 

The lantern burned up to full light as Caleb leapt up, scrambling for his shirt. Jester awoke with a start, rubbing the sleep and dried tears from her eyes as she inspected the ruckus. Caleb had flung himself from the bed and pulled his nightshirt on, only half-buttoned, and was staring daggers at the door with a blush-red face of deep concern. Jester slowly turned ‘round and locked eyes with Beau, who looked only mildly surprised. 

“You guys weren’t…” Beau gestured strangely with her hands, scowling as embarrassed blush burned across her cheeks.

“Whatever you think was happening… Beauregard, I’ll erase your memories… We weren’t doing anything--” Caleb’s frantic stammerings halted as Jester raised a hand.

“She knows about the hotel, Cayleb.” Jester’s eyes were puffy from crying and lack of sleep, and she yawned.

“We were just sleeping, ja?” Caleb muttered, all urgency replaced by embarrassment thinly-veiled as irritation.

“Yeah, whatever,” Beau waved him off, “whatever you guys do when you’re alone I don’t care and I don’t wanna know. I just wanted to make sure Jester was okay.”

“So you waited until the middle of the night to creep around the house and ask her, hmm?”

“For your information, Caleb, I woke up ‘cause I had to piss and she was gone. I looked everywhere before I came here. It’s always the last place you look…” Beau grumbled. 

Jester had to fake a cough to hide a laugh. They really did act just like brother and sister. 

“And you,” Beau growled as she suddenly found her train of thought, “you’re helping her aren’t you? You better’ve told her she t’ give it a rest with mothering everyone! Can’t you see she’s exhausted?”

“Beau, stop,” Jester whined, like a tired child, “Cayleb’s been lecturing me all night about sleeping and how I’m ‘not helping myself’ blah, blah, blah…” She trailed off as another yawn took her over.

“I love you both so much, but I’m really, really, real-ly tired. You can keep fighting, but just whisper because I’m going back to sleep.” Jester burrowed into Caleb’s bed without another word.   
Caleb and Beau exchanged glances, their eyes flicking between each other and Jester. 

“Well, it seems like you have everything handled,” Beau said with a huff, puffing her chest out and crossing her arms authoritatively.

“Ja, I do.” Caleb’s jaw clenched tightly. 

“I swear to the gods, Caleb, if you don’t keep an eye on her, I’ll beat the shit out of you.” Beau hissed.

“I know you will, Beauregard.” Caleb rolled his eyes and pulled his shirt off again. “Now get out of my room.”


	7. Flowers for my Love

Jester’s fingers ran through Caleb’s autumn-red hair in practiced motions. His hair was well past his chin these days; while he’d paid special attention to keeping a close-crop on his beard, he’d left his hair free to grow as it pleased. Jester was thrilled because she particularly liked the way he looked with his hair hanging around his face, the loose curls framing his cheekbones and accentuating his sharp features. She’d always been keen to play with his hair, but it was one of her especially-favorite expressions of attraction now. She’d begun twisting small braids near the nape of his neck some weeks ago, the small plaits now well-lost in the thick locks. Jester would find them occasionally while brushing through Caleb’s hair, and her fingers would linger there just a moment.

It had been some time since Caleb had done anything nice with his hair besides pulling it back with a length of string into a low ponytail. Come to think of it, the last time may have well been when he’d worn flowers in his hair. That really had been quite a while ago. 

Jester spent the afternoon helping Caduceus in his garden, and he gifted her a bounty of flowers. Some were small pansies and tansies in bright pinks and yellows. He’d sprinkled in some bell-shaped lilies no bigger than a fingernail, a selection of daisy blooms, and a single white rose. Jester happily took the bouquet from him and made her way inside for the evening. She sneaked into Caleb’s room where she set the flowers in a plain vase with some water and left them for later. 

When dinner was long gone and full tummies lead to tired eyes, the Nein made their ways to bed one by one. Jester stayed in the kitchen, dutifully scrubbing dishes. Soap clung to her arms above her elbows and spattered across her clothes, soaking her. Caleb often teased her, saying she looked a little too much like her alleged father. She’d often reply by splashing him with the dirty water.

When she’d dried her arms and abandoned her sopping apron, she retired to Caleb’s room. He’d gone for a wash in the MT Spa, so she took the time to abandon her wet clothes in exchange for Caleb’s underclothes and shirt. She quite liked his clothes - the ones he bought in Xhorhas were soft and comfortable, and they finally carried his scent. Wearing them relaxed her. 

Caleb returned from his bath a short time later with his hair up in a towel the way Caduceus had taught him. Jester thought he looked perfectly adorable, towel perched jauntily atop his head. He cast a glance at the flowers and raised his eyebrows at her. 

“What are those?” 

“Do you remember that one time that you wore flowers in your hair?”

“Mm.”

“I want to do that again!” Jester’s smile forced her eyes shut, and she flashed ivory-white teeth in a wide, toothy grin.

Caleb sighed, pretending to be beleaguered, but smiled wide as he plopped down on the bed and let his hair down. 

Jester combed his hair out, drying it best she could with the dry parts of the towel before she set to work braiding. She weaved and looped the strands into a lovely ‘do, pinning loose ends in place where she couldn’t force them into the braids. Then she set to work placing the flowers amongst the twists. Each stroke of her hand was delicate and deliberate, careful to place the flowers in a good place on the first go. A little while later she had Caleb looking like a blushing bride.

“Pass me the mirror, Blueberry,” Caleb said, reaching his hand toward the ornate glass on Jester’s bedside table. He hummed quietly as he admired himself, marvelling at Jester’s handiwork.

“You make me look so delicate.” Caleb turned to look her in the eyes. “How do I look?”

Jester was quietly blown away. Caleb was a handsome man, of this there was no doubt, but seeing him like this now made her heart drum. He was so striking - the contrast of the pale summer flowers against his bright hair softly curved around the stems, the way the shape of the braids complimented his angular face. His eyes seemed to stand out especially bright against the pansies, which Jester had trailed down his temples behind his ears, and the lilies that hung around his forehead like a circlet centered the look.

“You are so beautiful,” she whispered, a smile spreading across her face. 

“Right back at-cha.” Caleb winked, his accent giving the “cha” a hard emphasis. 

Jester cupped Caleb’s cheek in her hand, and he leaned into her. His eyes didn’t leave hers as he smiled and reached up to her hand.

“You are so precious to me, Jester,” he said softly, his voice barely a whisper. His eyes grew misty as they welled with tears. Jester wiped a stray tear from the corner of his eye and held his face with both hands. 

“That’s so embarrassing,” she whispered back, her smile turning to a cheeky grin, “you just said that to me! Oh my gosh, Cayleb, that’s so bold!”

“This will be very bold, then.” He leaned forward and kissed her, holding her face in his hands now. He smiled against her lips, and her heart fluttered. 

Jester pushed Caleb back and sat atop of him, straddling his hips. He awkwardly reached back and turned the lantern down as she pushed him down into the bed, pressing the flowers into the pillows.

“Oh.” Caleb reached up and pulled out a flower. “I should take these out--”

“No, leave them in. I want to keep looking at you, Cayleb,” Jester pleaded, pouting. 

“Of course, Liebling,” Caleb growled playfully before pulling Jester back down to him.

She gazed at him intently, determined not to forget a single detail. She wanted to remember this moment exactly as it was, this moment of pure and unadulterated beauty. It was easy to fix his face in her mind; she’d done it a million times. She didn’t even have to think to remember his face anymore - he was always there whenever her thoughts wandered back to him. 

This thought would be no different.


	8. Interlude 1 - Widojest Week Day 1: Healing - I Love You

**Notes for the Chapter:**

> Happy Widojest Week! I'm doing some writing and some drawing, so keep your eyes peeled for both. Much love, thank you for reading.

“I love you, Cayleb.”

When Caleb first met Jester, he didn’t think much of her. She was kind and beautiful, filled with youth and affinity for life. She was so far separated from Caleb he couldn’t imagine being close with her, even as friends. It had been years since he’d had someone he called a friend. 

No, that privilege had been wrenched from his hands the day he diverged from humanity.

When he’d admitted to Nott he viewed the Mighty Nein as his friends something inside him changed. Happiness bloomed from having found people who mattered to him and, more importantly, he mattered to. Fear - unspeakable, unimaginable fear. That too grew in his heart like a creeping weed. 

Over time he grew to understand his friends better and better. Beau was his partner in crime, his first confidant, maybe his best friend. He’d never had siblings, but he wondered if this is what it was like. Fjord was his brother in arms. It was easy to get caught up with his schemes, running the same train of thought off the beaten path with him. He’d gotten on nicely with Mollymauk. He trusted Yasha. She was his guide to interacting with people. She’d taught him to hug for gods’ sake! Nott, of course, was his savior, his most-trusted friend. He was there to protect her, and she in exchange took care of him when he couldn’t take care of himself. Caduceus had quickly become a friend, and Caleb was grateful for him at every turn. 

Jester…

Jester was kind. She always thought about others before herself, she saw the good in her friends, saw little reflections of them in the good parts of the world. Jester was happy. She was so full of joy, so quick to say a kind word to brighten someone’s day. If someone was sad, she was the first to tell a joke or do something silly to cheer them up. Jester was clever and funny. Mischievous, creative, cunning, quick-witted. Jester had a penchant for bringing laughter with her everywhere she went. Jester was innocent. She had lived so much life filled with love, living life for the people around her, loving herself just as she was. She may have read Caleb’s smutty books and killed a lot of monsters, but she was the best person Caleb knew by a long shot. She was too kind, too happy, too clever, too funny, too innocent -- too good. 

Far too good for Caleb. 

So, whatever this feeling was that welled in his chest at the mere thought of her, that was all it would ever be - a feeling. A secret thought, a moment of passing. A dream never to be realized. 

Caleb was quite shocked at Jester’s words.

Emotions flooded from his heart, fleeing like escaped prisoners running for their lives for fear of being encaptured once more. His heart pounded in his throat, ears, stomach. He felt faint. Confusion and uncertainty rushed through him, flooding his mind. It had been an accident. A careless statement, spoken on a whim. She didn’t mean it. She would be blushing now, waving her hands and stammering awkwardly to defend herself. It was all just an unfortunate slip of the tongue, and if they were lucky, they’d forget it in the morning.

Except that it wasn’t.

Jester’s eyes were earnest, not a glimmer of teasing in them. She was deathly serious, blushing, but not embarrassed. Nervous maybe, but honest and awaiting Caleb’s reply. 

“Jester…”

“I really do.” Caleb couldn’t look at her.

“Jester, don’t… You can’t… You don’t know anything about me. You can’t… say that,” Caleb stammered, struggling to find the words.

“I think I know you pretty well,” she argued.

“I am not a good person, Jester. I am a bad, bad person. You can’t say things like that without thinking, you’ll say something you regret.”

“That’s not true, Cayleb…” Jester trailed off for a moment. “You don’t know how I feel. I do, I really do.”

“You don’t.” Caleb’s voice was steady and cold. Tears burned in his eyes, and he gritted his teeth angrily.

“You don’t know that!” Jester’s eyes were filled with tears, her cheeks beet red.

“Even if you do, it is foolish. You shouldn’t. I am not worth those feelings, Jester, you’ll only end up regretting saying that to me. You can’t!” Caleb huffed, his face flushed and hot.

“Just forget about it,” he said.

“Cayleb--”

“Forget about it, Jester. I already have.”

That night, as Caleb lay alone in his bed, he cried silently. His shoulders didn’t shake, he wasn’t struggling to breath through snot and sobs. Tears simply made their way down his face, pooling along his nose and ears on their way to his pillow. Pain chewed at him, wearing on his heart. He could feel the weight of it deep inside him, like a disease making its first advances. It was unbearable.

He wiped his face dry with his dirty bandages and sat up from his bed. Nott was sound asleep across from him, thank the gods. This wasn’t something he wanted to talk to her about. Telling her about his childhood had been hard enough; he wasn’t keen to repeat that experience so soon if ever. Instead he quietly left the room and made his way to the bath. At this time of night, the bathrooms were totally empty. He sat in the corner across from the old wooden washtub and glared at his reflection in the makeshift mirror before him. 

“Look at you,” he began, his voice low and disapproving, “disgusting. What she could even see in you is a mystery. What would she think if she knew who you really were, what you’ve done? Bah.”

He rested his forehead against his knees and sighed as he examined the floor beneath him.

“She would run from you in terror, fast as the wind. They all will, eventually. Even Beauregard. Even… Even Nott. Who wouldn’t, of course…” He choked down a sob. “You are unlovable. Absolutely, completely, ineffably unlovable. So, go on, banish that fantasy. It is a pipe dream. It’s nothing. Grow up.”

“You are unlovable.”

“Absolutely… Unlovable… Bren Aldrich Ermundrud.”

Hot tears streamed down his face as he sobbed. What a sight he must be, a filthy man huddled in the corner of a destitute bathroom, crying his eyes out into bloody, dirty bandages. Over what? A truth he already knew? A foolish hope? A pointless, fruitless waste of his thoughts? Over Jester’s ignorance of just how disgusting he was, perhaps. This pain and longing in his heart was strong, but he couldn’t let it control him. He was desperate for love - to belong to someone again. To have a family. He didn’t deserve it, though. He couldn’t live through it again, fearing loss, failure, destruction… Trent had made sure of that. Astrid… She’d made sure of it too.

“Cayleb?”

Caleb leapt with a start at the sight of Jester standing in the bathroom doorway, the sleeve cuffs of her nightdress wet with tears. She didn’t look sad now, though, only concerned. Damn, he couldn’t just hurt her, he had to worry her too. What a mess.

“Jester, please leave--”

“No, Cayleb.” Jester’s voice was soft but resolute. “I’m not going to leave you.”

Caleb sat in silence as Jester crouched down next to him, vaguely aware of her tail flicking nervously back and forth behind him. He couldn’t bear all of this. He couldn’t sit here and let her bother herself with his silliness -- but then, she said she wouldn’t leave, and what could he say to that?

“I’m sorry, Cayleb,” Jester whispered, eyes focused on her bare feet, “I’m sorry life hasn’t been so kind to you.”

“It’s not--”

“I know it’s not my fault, but I’m still sorry, Cayleb. You’re my best friend, my family, I’m always going to worry about you, you know?” There was a certain peace and certainty in the sadness that drenched Jester’s words that comforted Caleb, much to his surprise.

“I was wrong to push you away,” Caleb said, his voice gruff from the tightness in his throat.

“You know,” Jester said softly, “it gets easier. Living after something sad happens.”

“How do you know that?” Caleb scoffed, but only just. If Jester had answers, he would gladly take them.

“You’re not the only person in the whole world who’s ever suffered, Cayleb,” Jester laughed sadly, still staring mindlessly at her feet. “Everyone’s hurt at some point, even me.”

Caleb sat in silence, considering how foolish he’d been to assume Jester couldn’t understand. Of course she’d suffered in her life. They all had, he’d just been too stubborn and self-centered to realize it. It was hard to see past your own depravity when you were drowning in it. Naturally, he’d assumed the others weren’t even swimming in that terrible sea - only they had been, just out of sight. 

“But it does get easier.” Caleb believed her. “And I promise I won’t leave you while you heal, Cayleb. You’re my best friend, and I love you, and what kind of cleric would I be if I didn’t help you heal?”

“Thank you, Jester.”

He hesitated for a moment. 

“I love you, too.”


	9. Interlude 2 - Widojest Week Day 5: There’s Only One Bed - The Fools’ Reward

**Notes for the Chapter:**

> Some more Widojest Week madness! Again, so many thanks to goggles-girl for this. Kiki you’re such a big encouragement!!

“Okay, Jester, we can find a way to make this work, ja?”

Caleb stared down the single small bed before him as if it were an unfamiliar enemy, an unpredictable wildcard. How this had happened, Caleb hadn’t the faintest idea, but now he was faced with solving the problem. Simple enough, he could sleep on the floor. Except Jester wouldn’t stand for that - this place was, in all honesty, the coldest place he’d ever been. Stone floors in a city that never saw summer? What kind of madness! While he couldn’t die from the cold, he’d be miserable from it and Jester simply wouldn’t allow that.

What, then, could be done except share?

Jester, still wearing most of her traveling clothes, had tucked herself in neatly, her legs resting slightly off the mattress atop her pack and outer coat. Caleb removed his filthy jacket and books before carefully settling into the small, lumpy bed. He’d rejected the pillow; Jester deserved it if she was going to put up with all this. Besides, Frumpkin had proven time and time again his usefulness as a pillow and was perfectly fit for the job. 

Caleb blew out the lamp on his nightstand and settled in awkwardly, intensely focused on keeping every inch of his body at least a finger’s width away from Jester. Just as he began to relax, Jester sighed and rolled over, causing him to reflexively tense and shift away from her. He did so in vain, however, as Jester casually sprawled beside him, her arms resting on his side as she peered over to check on him.

“I didn’t wake you, did I, Cayleb?” she asked in a loud whisper. If he had been asleep she certainly would have woken him.

“Ah, no, Jester, you did not.”

“Oh, good!” She flopped back down beside him, granting him some momentary relief.

“Do you ever think about how crazy it is that we met? I mean, me and Fjord and Beau were like, ‘Ooh, heroes, travellers, noble causes, let’s go kill stuff for money!’ and all, but meeting everyone else was the craziest chance ever, you know?” Jester had a proclivity to ramble, especially when she was telling stories or recounting relatively-unimportant goings-on. Caleb didn’t mind the rambling, though, because it meant he didn’t have to try awkwardly to fill the silence. It helped too that he rather liked Jester and enjoyed hearing her talk.

“And, like, what would we even be doing right now if we hadn’t met? You’d probably be a stinky little man, stinking around in pubs and rolling in the mud.”

“I have never once rolled in mud,” Caleb said, glancing at Jester. He could only just make out her profile in the dark, but he had a feeling she had a toothy grin on her face.

“O--kay, Cayleb, it just seems like something you might do if you hadn’t met us,” Jester sighed, seemingly exasperated with her bedmate.

“If I had not been enlightened by you clean people, ja?” he teased.

“Exactly! Now you understand. So anyways…” Jester continued on, considering all the things each member of the Mighty Nein would hypothetically be doing if they’d stayed in their smaller groups. Ultimately, the alternate future was far duller than reality; however, in her typical fashion, Jester did imagine some rather fantastical possibilities as well.

“... and what if you and Nott fell in love? Hoh, that would be so weird!” Jester grimaced at the thought, sticking her forked tongue out emphatically.

“Wha-- Jester, Nott and I would not have, what did you say, ‘fall in love’?” Caleb seemed offended at the thought.

“I didn’t say it would happen, just that it would be so creepy if it did!” 

Caleb rolled his eyes. “Is there not anyone else I could have fallen in love with, oh great seer?”

“I don’t know, Caleb, I think pretty much everyone else is wa--ay too clean for you,” Jester giggled.

That got Caleb. He chuckled and turned on Jester, suddenly wide awake and ready to banter. 

“I do not know, Blueberry, I don’t think you are so clean either!” he laughed as she gasped, shocked.

“Cayleb! That was so mean!” she howled as she battered Caleb with an unexpected swing of her pillow. 

He took the first hit square in the face, but prepared too well for the second by snatching it from her hands. He used the pillow as a shield and went in to barrage her with pokes to her sides. She screamed as she tried in vain to dodge his hands, finally giving up and letting Caleb tickle her until she couldn’t breathe. Caleb dropped the pillow and went in for a fully-fledged assault. He didn’t stop until Jester hit him on the arm to “tap out.” She grabbed his shoulder and sat up, using him to steady herself as she recovered her breath. Caleb couldn’t see her face, not well at least, but he could feel her breath on his face. 

In a moment, laughing became nervous kissing as Jester leaned in. Caleb let out a surprised grunt but kissed her back. He was shocked, but he hadn’t seen the way Jester had looked between his eyes and lips, her heart light and optimistic from laughter and wanting something more. She giggled nervously as she pulled away from the short but sweet kiss.

“I’m sorry, Cayleb, I just--” she cut off as Caleb kissed her.

Their hands found purchase in each other’s hair, and their breathing suddenly grew rough. Jester’s lips tasted of alcohol, her teeth were sharp against his lips, and her split tongue felt strange, but none of it was remotely unpleasant. She must have felt the same because she let her hands stray to his chest and, a short moment later, hips. Caleb’s heart was racing -- they were being incredibly foolish, but he didn’t want to stop if she wasn’t. 

When they lay side by side, spent and drenched in sweat, Caleb thought about how insane the situation was. It was one thing to give in to a moment of passion, but another entirely to be lying naked beside one of your best friends after impromptu sex. The stress of it all rose in his chest, and he felt his throat tighten as his lungs refused to breathe normally. He relaxed suddenly as Jester’s hand found his, her fingers gently lacing between his. 

“Hey, Cayleb,” she said softly, “so, we just, um…”

“Ja,” Caleb sighed.

“Did you, um, I mean, did you… actually… want to do that?”

“Ah…” Caleb paused, thinking. His next words were critical: he needed to be honest, but what was the honest answer to that question? He hadn’t really seriously considered his romantic feelings for Jester past acknowledging them. It wasn’t as if he’d planned tonight’s events, in fact it hadn’t even crossed his mind as an insanely-best-scenario possibility. So what could he say?

“Ja… I think, in a way, I have… had feelings for you for some time. Maybe not… this specifically… but I have certainly thought of you in this light for a while. Does that answer your question?”

Jester laughed softly. “Yes, Cayleb, that’s good.”

“You wanna know the truth?” she asked, her voice barely more than a whisper.

“Mhm.”

“I really wanted to do that. Like, not in a creepy way or anything! I just, you know, after you had a bath, and cut your hair, and got that new coat, and after Yasha taught you how to act normal, I dunno we became friends and then I was like, ‘Oh my god, do I like him?’ and then I was like, ‘Oh my god, I really like him!’ and then… Ugh! I like you a lot, Cayleb, I don’t wanna sound like a weirdo, but I really really really liked you, maybe even since that first time we met last year, and I wanted to tell you, but I didn’t want to freak you out ‘cause you’re always like, ‘I don’t want you guys to like me ‘cause I’m a bad person or whatever, huh huh huh--’ “

“Is that really what I sound like?” he laughed, “ ‘Huh huh huh’?”

“Cay-leb, ple-ase,” Jester whined, “I’m trying to say I’m not a creepy weirdo and I liked you a normal amount before I wanted to bone you.”

Caleb couldn’t see her face, but if he had, he knew she’d be blushing so brightly as if she were sunburned. 

“Is that how it is, then?” he asked, his voice tinged with laughter. 

“Hmmaybeee…” Jester muttered, embarrassed.

“That is good news, then, Blueberry.”

“It is?” she exclaimed.

“Ja, it means I am a likeable person besides being ‘totally bone-able.’ “

“Cayleb!”

He laughed.


End file.
